Dimethylformamide → 6-Chloropyrimidine-4-carbonyl chloride

HRID 2202072Notes

Reaction equation

HRID 2202072 reaction equation
CN(C=O)C.[Cl:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([C:13]([OH:15])=O)[CH:8]=1.C(Cl)(C([Cl:20])=O)=O>C(Cl)Cl>[Cl:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([C:13]([Cl:20])=[O:15])[CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 166377476-Chloro-4-pyrimidinecarboxylic acid

Product 1

HCID 184220986-Chloropyrimidine-4-carbonyl chlorideYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A drop of DMF was added to a stirred solution of 6-chloropyrimidine-4-carboxylic acid (5.5 g, 34.7 mmol) and (COCl)2 (12 mL) in DCM (100 mL). The mixture was stirred at 25° C. for 2 h. The solvent was evaporated under reduced pressure to give crude 6-chloropyrimidine-4-carbonyl chloride (6.0 g, yield: 97.7%). 1H NMR (400 MHz, DMSO-d6) δ 9.20 (s, 1H), 8.10 (s, 1H).

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5330bd9c98e74410bd6c09667f255c04
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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